Direct Catalytic Asymmetric Mannich-Type Reaction of Alkylamides

被引：39

作者：

Arteaga, Fernando Arteaga ^{[1
]}

Liu, Zijian ^{[1
]}

Brewitz, Lennart ^{[1
]}

Chen, Jianyang ^{[1
]}

Sun, Bo ^{[1
]}

Kumagai, Naoya ^{[1
]}

Shibasaki, Masakatsu ^{[1
]}

机构：

[1] Inst Microbial Chem Bikaken, Shinagawa Ku, 3-14-23 Kamiosaki, Tokyo 1410021, Japan

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 10期

关键词：

ALDOL REACTION; 1,4-ADDITION REACTIONS; BETA-PEPTIDES; AMIDES; ALDEHYDES; ALKYLNITRILES; ACETONITRILE; THIOAMIDES; COMPLEXES; IMINES;

D O I：

10.1021/acs.orglett.6b00879

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Direct enolate formation coupled with subsequent enantioselective C-C bond formation remains a topic of intense interest in asymmetric catalysis. This methodology is achieved even with low acidic amides without an electron-withdrawing group at the alpha-position in the context of a Mannich-type reaction. Acetate-, propionate-, and butyrate-type 7-azaindoline amides served as enolate precursors to afford the desired Mannich adducts with high stereoselectivity, and ligand-enabled diastereo-divergency provided access to both anti/syn diastereomers. The facile transformation of the amide moiety ensures the synthetic utility of the Mannich adducts.

引用

页码：2391 / 2394

页数：4

共 50 条

[21] Mechanistic studies on the catalytic asymmetric Mannich-type reaction with dihydroisoquinolines and development of oxidative Mannich-type reactions starting from tetrahydroisoquinolines
Dubs, Christian
Hamashima, Yoshitaka
Sasamoto, Naoki
Seidel, Thomas M.
Suzuki, Shoko
Hashizume, Daisuke
Sodeoka, Mikiko
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (15): : 5859 - 5871
[22] Stereodivergent Direct Catalytic Asymmetric Mannich-Type Reactions of α-Isothiocyanato Ester with Ketimines
Lu, Gang
Yoshino, Tatsuhiko
Morimoto, Hiroyuki
Matsunaga, Shigeki
Shibasaki, Masakatsu
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (19) : 4382 - 4385
[23] Catalytic Asymmetric Mannich-Type Reaction of N-Alkylidene-α-Aminoacetonitrile with Ketimines
Lin, Shaoquan
Kawato, Yuji
Kumagai, Naoya
Shibasaki, Masakatsu
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (17) : 5183 - 5186
[24] Catalytic Asymmetric Three-Component Mannich-Type Reaction of Alkenyl Trichloroacetates
Izumiseki, Atsuto
Yoshida, Kazuhiro
Yanagisawa, Akira
ORGANIC LETTERS, 2009, 11 (22) : 5310 - 5313
[25] Catalytic Asymmetric Mannich-Type Reaction Enabled by Efficient Dienolization of α,β-Unsaturated Pyrazoleamides†
Zhang, Hai-Jun
Zhong, Feng
Xie, Yan-Cheng
Yin, Liang
CHINESE JOURNAL OF CHEMISTRY, 2021, 39 (01): : 55 - 61
[26] Catalytic Asymmetric Vinylogous Mannich-type (AVM) Reaction of Nonactivated α-Angelica Lactone
Zhou, Lin
Lin, Lili
Ji, Jie
Xie, Mingsheng
Liu, Xiaohua
Feng, Xiaoming
ORGANIC LETTERS, 2011, 13 (12) : 3056 - 3059
[27] The catalytic asymmetric Mannich-type reactions in aqueous media
Kobayashi, S
Hamada, T
Manabe, K
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (20) : 5640 - 5641
[28] Direct Catalytic Asymmetric Mannich-Type Reaction of Benzyl Isocyanide: Stereoselective Synthesis of 1,2-Diarylethylenediamines
Tamura, Keiji
Kumagai, Naoya
Shibasaki, Masakatsu
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (14) : 3026 - 3031
[29] Direct asymmetric catalytic Mannich reaction
Zhang, YW
Wang, JF
Shen, ZX
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2003, 23 (11) : 1324 - 1329
[30] The direct catalytic asymmetric Mannich reaction
Córdova, A
ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (02) : 102 - 112

← 1 2 3 4 5 →